Water → 2-amino-3-nitro-N-tosylaniline

HRID 2081898Notes

Reaction equation

HRID 2081898 reaction equation
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.O>N1C=CC=CC=1>[NH2:11][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][C:6]=1[NH:10][S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 141475022-amino-3-nitro-N-tosylaniline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.1 mol (15.3 g) of 3-nitro-ortho-phenylenediamine is dissolved in 50 ml of pyridine, and 0.11 mol (21 g) of para-toluenesulphonyl chloride is then added gradually, whilst stirring, at between 40° and 45° C. When the addition has ended, the stirring is maintained for 15 minutes and the reaction medium is then poured into 250 ml of iced water. The expected product precipitates. It is filtered off, washed with water and recrystallised from acetic acid. It melts at 195° C.

Workup

  1. additionWhen the addition
  2. temperaturethe stirring is maintained for 15 minutes
  3. customThe expected product precipitates
  4. filtrationIt is filtered off
  5. washwashed with water
  6. customrecrystallised from acetic acid

Sources & evidence

ORD record
ord-4345857661af4006b4d35c00cb8546bc
Source dataset
uspto-grants-1993_02
Patent number
US05186717

Reaction notes

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